US3890248A - Catalytic oxide adapted for the preparation of unsaturated carbonyl compounds - Google Patents
Catalytic oxide adapted for the preparation of unsaturated carbonyl compounds Download PDFInfo
- Publication number
- US3890248A US3890248A US392500A US39250073A US3890248A US 3890248 A US3890248 A US 3890248A US 392500 A US392500 A US 392500A US 39250073 A US39250073 A US 39250073A US 3890248 A US3890248 A US 3890248A
- Authority
- US
- United States
- Prior art keywords
- catalyst
- catalytic oxide
- catalytic
- unsaturated carbonyl
- carbonyl compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 24
- 150000001728 carbonyl compounds Chemical class 0.000 title abstract description 11
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 8
- 239000000470 constituent Substances 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 abstract description 7
- 230000003647 oxidation Effects 0.000 abstract description 5
- 238000007254 oxidation reaction Methods 0.000 abstract description 5
- 239000012808 vapor phase Substances 0.000 abstract description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910020598 Co Fe Inorganic materials 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 4
- 239000000347 magnesium hydroxide Substances 0.000 description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 2
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- -1 olefin metal oxide Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- RDQSSKKUSGYZQB-UHFFFAOYSA-N bismuthanylidyneiron Chemical compound [Fe].[Bi] RDQSSKKUSGYZQB-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/888—Tungsten
- B01J23/8885—Tungsten containing also molybdenum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
Definitions
- This invention relates to a catalyst composition in a catalytic oxide, specifically adapted for use in a process for the preparation of unsaturated carbonyl compounds from olefins. More particularly, the invention relates to such catalytic oxide useful for the preparation of the corresponding unsaturated carbonyl compounds, for example, acrolein and acrylic acid, by the catalytic vapor phase oxidation of olefins having at least three carbon atoms.
- a catalytic oxide compound of molybdenum, tellurium, cadmium or zinc, and oxygen is recommended, for example, by the prior art disclosed in lapanese Official Pat. Gazette, Publication No. 10605/68. Also the same Gazette, Publication No. 6245/69 teaches the use ofa catalytic oxide composed of nickel, cobalt, iron bismuth, molybdenum, phosphorus and oxygen.
- per-pass yields of the unsaturated carbonyl compounds obtained through the use of such known catalysts are far from satisfactory in commercial operation.
- a catalyst composition i.e., catalytic oxide specifically adapted for use in a process for producing unsaturated carbonyl compounds with industrial advantage.
- the catalyst or catalytic oxide of the present invention is characterized in that its constituent elements are present at atomic ratios satisfying the following: Co:- Fe:Bi:W:Mo:Si:Z 2.020.0 0.l-l0.0 0.l-l0.0 0.5l0.0 2.0-1 l.5 O-15.0 0.005-l.0 (provided that W Mo 12.0, and Z represents an alkaline earth metal; i.e., Be, Mg, Ca, Sr, Ba or Ra).
- W Mo 12.0, and Z represents an alkaline earth metal; i.e., Be, Mg, Ca, Sr, Ba or Ra).
- the oxygen is present in the catalyst in the form of complex Conversion Selectivity (7) Per-pass yield (7) Mol number of reacted olefin metal oxide or metallic acid salt. Consequently, the oxygen content of the catalyst varies depending on the atomic ratios of the metallic elements constituting the catalyst.
- the catalyst of the invention can be prepared through the steps of, for example, mixing an aqueous solution of ammonium p-tungstate, adding to the mix ture aqueous solutions of, respectively, cobalt nitrate, iron nitrate, and bismuth nitrate, further adding thereto an aqueous solution of a hydroxide or carbonate of an alkaline earth metal and if desired, subsequently adding colloidal silica as a silicon source, concentrating the system by evaporation, molding the resulting clay-like substance and calcining the same at temperatures between 350600C, in an air current.
- the starting materials of the catalyst are not limited to the ammonium salt, nitrate, hydroxide and carbonate as stated above, but other various compounds are equally useful as long as they can form the catalytic oxide upon calcination.
- silica gel, alumina, silicon carbide, diatomaceous earth, titanium oxide and Celite, etc. may be employed, particularly preferred carriers being silica gel, titanium oxide and Celite.
- the catalytic vapor phase oxidation using the catalytic oxide of the invention is performed by introducing a gaseous mixture composed of l-l0 volume percent of an olefin such as propylene, 5-15 volume percent of molecular oxygen, 20-60 volume percent of steam and 20-50 volume percent of an inert gas, onto the catalyst prepared as above, at temperatures ranging from 240450C, and pressures ranging from the normal atmospheric pressure to 10 atmospheres. Suitable contact time ranges from 1.0 to 10.0 seconds.
- the reaction can be carried out either with a fixed bed or a fluidized bed.
- the excellent results of the present process are presumably due to the appropriate adjustment of catalytic ability accomplished by the concurrent presence, in the catalytic oxide of the invention, of molybdate and tungstate of cobalt, iron and bismuth, with oxides; and presence of heteropolyacid compounds containing silicon and the alkaline earth metal, etc.
- This presumption is substantiated by the fact that the selectivities are markedly improved by the presence of the alkaline earth metal, as demonstrated in the Control which appears hereinafter.
- EXAMPLE 1 Seventy grams of cobalt nitrate were dissolved in 20 ml of distilled water. Also 24.3 grams of ferric nitrate were dissolved in 20 ml of distilled water, and 29.2 grams of bismuth nitrate were dissolved in 30 ml of distilled water, which was made acidic with 6 ml of concentrated nitric acid. Separately, in 150 ml of water, 106.2 grams of ammonium molybdate and 32.4 grams of ammonium p-tungstate were dissolved under heating and stirring.
- the catalyst was used in the reaction of Example 1, with the results as shown in the subsequent Table.
- EXAMPLE 5 A catalyst of the composition in terms of atomic ratio: Co Fe Bi W Mo Si Ca was prepared in accordance with the procedure of Example 1. Using the catalyst, the reaction was carried out under the same conditions as in Example 1. The results were as shown in the subsequent Table.
- EXAMPLE 6 A catalyst of the composition in the terms of atomic ratio: Co Fe Bi W Mo Si 5Ba was prepared in a manner similar to Example 1, except that 0.941 gram of barium nitrate was used instead of 0.21 gram of magnesium hydroxide.
- This catalyst was used in the reaction of Example 1, with the results as shown in the subsequent Table.
- CONTROL Example 1 was repeated, except that the use of magnesium hydroxide was omitted.
- the composition of the resulting catalyst was as follows, in terms of atomic ratio: CO Fe Bi W2MO oSi 35.
- This catalyst was used in the reaction of Example 1, with the results as given in the following Table.
- EXAMPLE 4 A catalyst of the composition in terms of atomic racatalytic oxide in which the atomic ratio among the constituent elements Co:Fe:Bi:W:Mo:Si:Z is within the range of 2.020.0 0.ll0.0 0.ll0.0 0.5-10.0:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US392500A US3890248A (en) | 1970-12-26 | 1973-08-29 | Catalytic oxide adapted for the preparation of unsaturated carbonyl compounds |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11878970 | 1970-12-26 | ||
US00211680A US3799978A (en) | 1971-12-23 | 1971-12-23 | Process for the preparation of unsaturated carbonyl compounds |
US392500A US3890248A (en) | 1970-12-26 | 1973-08-29 | Catalytic oxide adapted for the preparation of unsaturated carbonyl compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
US3890248A true US3890248A (en) | 1975-06-17 |
Family
ID=14745116
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US392500A Expired - Lifetime US3890248A (en) | 1970-12-26 | 1973-08-29 | Catalytic oxide adapted for the preparation of unsaturated carbonyl compounds |
Country Status (10)
Country | Link |
---|---|
US (1) | US3890248A (nl) |
BE (1) | BE777263A (nl) |
CA (1) | CA956971A (nl) |
CS (1) | CS178092B2 (nl) |
DE (1) | DE2161471C3 (nl) |
FR (1) | FR2119763A5 (nl) |
GB (1) | GB1346626A (nl) |
IT (1) | IT944129B (nl) |
NL (1) | NL149477B (nl) |
PL (1) | PL85157B1 (nl) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4264476A (en) * | 1978-10-20 | 1981-04-28 | Ube Industries, Inc. | Catalyst for producing acrylonitrile in a fluidized bed reactor |
US4487849A (en) * | 1982-07-29 | 1984-12-11 | Monsanto Company | Catalyst for the reverse disproportionation process |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1426303A (en) * | 1972-08-25 | 1976-02-25 | Ube Industries | Catalyst and process for oxidation of ammoxidation of olefin mixtures |
GB1523772A (en) * | 1974-07-22 | 1978-09-06 | Standard Oil Co | Oxidation catalysts |
US4778930A (en) * | 1974-08-05 | 1988-10-18 | The Standard Oil Company | Process for the oxidation of olefins using catalysts contaning antimony |
CA1046491A (en) * | 1974-09-03 | 1979-01-16 | Union Carbide Corporation | Oxidation catalyst and process for preparing unsaturated acids and aldehydes |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3642930A (en) * | 1968-12-30 | 1972-02-15 | Standard Oil Co Ohio | Process for the manufacture of isoprene from isoamylenes and methyl butanols and catalyst therefor |
US3766092A (en) * | 1970-01-31 | 1973-10-16 | Asahi Chemical Ind | Catalyst for preparation of unsaturated nitriles |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3522299A (en) * | 1965-11-17 | 1970-07-28 | Nippon Kayaku Kk | Process for the oxidation of olefins to aldehydes and acids and catalyst therefor |
US3965166A (en) * | 1969-01-29 | 1976-06-22 | Celanese Corporation | Oxidation of olefins |
DE2125032C3 (de) * | 1970-05-26 | 1979-11-22 | Nippon Catalytic Chem Ind | Verfahren zur Herstellung von (Meth) Acrolein neben geringen Mengen (Meth) Acrylsäure |
-
1971
- 1971-12-10 DE DE2161471A patent/DE2161471C3/de not_active Expired
- 1971-12-15 GB GB5825071A patent/GB1346626A/en not_active Expired
- 1971-12-18 IT IT32612/71A patent/IT944129B/it active
- 1971-12-22 PL PL1971152403A patent/PL85157B1/pl unknown
- 1971-12-22 NL NL717117680A patent/NL149477B/nl not_active IP Right Cessation
- 1971-12-23 CA CA131,051A patent/CA956971A/en not_active Expired
- 1971-12-23 CS CS8960A patent/CS178092B2/cs unknown
- 1971-12-24 BE BE777263A patent/BE777263A/xx not_active IP Right Cessation
- 1971-12-27 FR FR7146797A patent/FR2119763A5/fr not_active Expired
-
1973
- 1973-08-29 US US392500A patent/US3890248A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3642930A (en) * | 1968-12-30 | 1972-02-15 | Standard Oil Co Ohio | Process for the manufacture of isoprene from isoamylenes and methyl butanols and catalyst therefor |
US3766092A (en) * | 1970-01-31 | 1973-10-16 | Asahi Chemical Ind | Catalyst for preparation of unsaturated nitriles |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4264476A (en) * | 1978-10-20 | 1981-04-28 | Ube Industries, Inc. | Catalyst for producing acrylonitrile in a fluidized bed reactor |
US4487849A (en) * | 1982-07-29 | 1984-12-11 | Monsanto Company | Catalyst for the reverse disproportionation process |
Also Published As
Publication number | Publication date |
---|---|
IT944129B (it) | 1973-04-20 |
NL7117680A (nl) | 1972-06-28 |
DE2161471B2 (nl) | 1974-01-24 |
CS178092B2 (nl) | 1977-08-31 |
DE2161471C3 (de) | 1982-05-13 |
GB1346626A (en) | 1974-02-13 |
DE2161471A1 (de) | 1973-07-05 |
BE777263A (fr) | 1972-04-17 |
CA956971A (en) | 1974-10-29 |
FR2119763A5 (nl) | 1972-08-04 |
PL85157B1 (nl) | 1976-04-30 |
NL149477B (nl) | 1976-05-17 |
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